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Preparation method of sulfuryl fluoride compound

A technology of sulfonyl fluorides and compounds, which is applied in the field of chemical synthesis, can solve the problems such as the difficulty in preparing the raw material sodium sulfinate, and achieve the effects of easy large-scale production, good compatibility, and mild reaction conditions

Inactive Publication Date: 2015-12-30
XINYANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Equally, this method needs anhydrous condition, and raw material sodium sulfinate is difficult to prepare ( Tetrahedron Lett .2009, 50, 3391)

Method used

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  • Preparation method of sulfuryl fluoride compound
  • Preparation method of sulfuryl fluoride compound
  • Preparation method of sulfuryl fluoride compound

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preparation example Construction

[0055] More specifically, the invention discloses a method for preparing sulfonyl fluoride compounds, comprising the following steps:

[0056] a), dispersing the sulfonyl hydrazide compound with the structure (I) and the fluorine reagent in a solvent;

[0057]

[0058] b), to the mixture obtained in step a) at 0-100 o Reaction at temperature of C for 2-18h to obtain sulfonyl fluoride compounds containing even structure (II);

[0059]

[0060] Among them, R 1 is aryl, substituted aryl, alkyl or substituted alkyl;

[0061] Preferably, the R 1 When it is an aryl group, it can be divided into phenyl, naphthyl or thienyl;

[0062] Preferably, the R 1 For substituted aryl, p-chlorophenyl, p-methylphenyl, p-nitrophenyl, p-methoxyphenyl, p-trifluoromethylphenyl, p-tert-butylphenyl, p-fluorophenyl , p-acetamidophenyl, 4-chloro-3-nitrophenyl, p-iodophenyl, p-trifluoromethoxyphenyl, p-n-propylphenyl, nitrophenyl, mesityl, 4-methyl-3-fluorophenyl or 3-bromo-5-trifluoromethylp...

Embodiment 1

[0071] In a clean and dry 10 ml Schlenk reaction tube, add 46.5 mg of p-toluenesulfonyl hydrazide, 1-chloromethyl-4-fluoro-1,4-diazobicyclo2.2.2-octanebis( Tetrafluoroborate) 177 mg, and use 2 milliliters of water as reaction solvent, 25 o C stirred the reaction for 2 hours. After the reaction, it was extracted by adding ethyl acetate, and the upper organic phase was directly spin-dried and dissolved with a small amount of petroleum ether and ethyl acetate (volume ratio: 30:1), and separated by a short silica gel column to obtain 34.8 mg of white solid , 80% yield.

[0072] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 1a As shown, the carbon NMR spectrum is as Figure 1b As shown, the NMR fluorine spectrum is shown as Figure 1c Shown; It can be confirmed from the spectrum that the product obtained is p-toluenesulfonyl fluoride.

Embodiment 2

[0074] In a clean and dry 10 ml Schlenk reaction tube, add 46.5 mg of p-toluenesulfonyl hydrazide, 1-chloromethyl-4-fluoro-1,4-diazobicyclo2.2.2-octanebis( Tetrafluoroborate) 97 mg, and use 2 milliliters of water as reaction solvent, 25 o C stirred the reaction for 8 hours. After the reaction, it was extracted by adding ethyl acetate, the upper organic phase was directly spin-dried and dissolved with a small amount of petroleum ether and ethyl acetate (volume ratio: 30:1), separated by a short silica gel column to obtain 30.5 mg of white solid , yield 70%.

[0075] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 1a As shown, the carbon NMR spectrum is as Figure 1b As shown, the NMR fluorine spectrum is shown as Figure 1c shown. It can be confirmed from the spectrum that the obtained product is p-toluenesulfonyl fluoride.

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Abstract

The invention relates to a preparation method of a sulfuryl fluoride compound. A sulfonyl hydrazide compound and a fluoride reagent serve as reaction raw materials. The preparation method includes the steps that a, the sulfonyl hydrazide compound with the structure (I) and the fluoride reagent are dispersed in a solvent, wherein the structure (I) is shown in the specification; b; a mixture obtained from the step a is stirred and heated to obtain the sulfuryl fluoride compound with the structure (II), wherein the structure (II) is shown in the specification (II). Compared with existing related technologies in the chemical synthesis field, the method of preparing sulfuryl fluoride from sulfonyl hydrazide is achieved for the first time. In the method, no catalyst needs to be added, reaction conditions are moderate, good compatibility can be achieved for water and air, and large-scale production is easy to achieve. The experimental result indicates that the yield of the obtained sulfuryl fluoride compound can reach up to 98%.

Description

technical field [0001] The invention belongs to the field of chemical synthesis. Specifically, the present invention relates to a preparation method of sulfonyl fluoride compounds. Background technique [0002] Sulfonyl fluorides are not only an important class of electrophiles in organic synthesis, but also can perform addition reactions with many nucleophiles ( J.Chem.Soc.PerkinTrans .21988,1919; J. Fluorine Chem .2010,131,248), is also an important free radical fluorinating reagent, recently Doyle et al. used pyridinesulfonyl fluoride as a fluorinating reagent to fluorinate fatty alcohols ( J.Am.Chem.Soc .2015, 137, 9571). More importantly, it widely appears in many bioactive molecules ( Chem. Biol .2013,20,541; J. Med. Chem. 2012,55,10995), are also widely used as 18 The labeling reagent of F has achieved a series of exciting results ( J.Am.Chem.Soc. 2008, 36, 12045; J. Am. Chem. Soc. 2013, 135, 5656). [0003] However, unfortunately, at present, sulfonyl fl...

Claims

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Application Information

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IPC IPC(8): C07B45/04C07C303/02C07C309/86C07C309/87C07C309/80C07C309/81C07D333/34
Inventor 唐林赵祥华杨性坤周玉强周国栋
Owner XINYANG NORMAL UNIVERSITY
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